Timeline: Looking back on Jaylen Brown’s Celtics career

After 10 seasons, 816 games, five All-Star appearances, and an NBA championship, Jaylen Brown’s time in Boston is over.

The Celtics traded their star wing to Philadelphia on Wednesday, finally breaking up the duo of Brown and Jayson Tatum after nine seasons together.

Brown’s time in Boston had some very high highs and some occasional lows. Here’s a look back on his decade in green.

June 23, 2016 — The beginning: The Celtics took Brown out of California with the third pick in the 2016 NBA Draft, a selection that wasn’t entirely popular at the time.

When then-owner Wyc Grousbeck announced the pick at an event for season-ticket holders, he was booed by fans that either wanted Providence’s Kris Dunn or for the team to package the pick in a trade for a star.

“Fourteen years, that’s probably the worst [reception] that I’ve gotten,” Grousbeck said. “We’re a bunch of fans who bought this team, and being a fan means you’re emotional, you’re emotionally invested in this team, and no problem. I actually believe [if] they knew what I knew, and we’re in the room, I think most of them might have done the same thing [in drafting Brown].”

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Oct. 26, 2016 — Debut in green: Brown played his first game for the Celtics in the 2016-17 opener, scoring 9 points on 3 of 4 shooting in a win over the Nets. He’d go on to make his first start on Nov. 3, scoring 19 points in a loss to the Cavaliers.

Brown made 20 starts in his rookie year, helping Boston to a 53-29 record and a trip to the Eastern Conference finals. He was named to the All-Rookie second team.

Oct. 17, 2017 — The Jays Era begins: The Celtics made another big pick at No. 3 in 2017, drafting Jayson Tatum to begin a partnership that lasted nearly a decade.

The two made their regular-season debut together (and started together) in the 2017-18 opener, a game remembered more for Gordon Hayward’s devastating leg injury in his own Celtics debut.

Brown had a career-high 25 points in the loss on the road to Cleveland. Tatum had 14.

April 17, 2018 — Playoff breakout: After the Celtics went 55-27 and finished second in the East, Boston beat Milwaukee in seven games in the first round, winning Game 2 behind 30 points from Brown. He became the youngest Celtic ever to score 30 in a playoff game in the process.

The Celtics lost to the Cavaliers in seven games in the Eastern Conference finals.

Oct. 21, 2019 — A big contract and a big breakthrough —The Celtics signed Brown to a four-year, $115 million extension before the 2019-20 season, a move that was widely considered an overpay after Brown struggled during the previous season.

Brown responded with a breakout year, averaging career-highs in points (20.3), rebounds (6.4), and assists (2.1) as he and Tatum took the reins after Kyrie Irving’s departure.

Brown narrowly missed out an on All-Star appearance that year, but earned those honors in five of the next six seasons.

Feb. 24, 2021 — First All-Star Game: A few weeks after crossing the 40-point threshold for the first time with 42 against the Grizzlies, Brown made his first All-Star team. He finished that season averaging 24.7 points, 6 rebounds, and 3.4 assists.

Boston struggled through that season, going just 36-36 in a pandemic-shortened year. The Celtics lost to the Nets in five games in the first round of the playoffs without Brown, who tore a ligament in his wrist with just a few games left in the year.

Jan. 2, 2022 — First 50-point game: Brown had two career outings in the first eight days of 2022, pouring in a career-high 50 points in a win over the Magic before notching his first career triple-double in a Jan. 8 win over the Knicks.

Jan. 31, 2022 — An energy shift: The Celtics’ first few months under Ime Udoka were underwhelming, with Boston mired in the doldrums of .500 basketball. In the hours before the Celtics took on the Heat at TD Garden, Brown authored a brief but now-iconic tweet: “The energy is about to shift.”

He was right. The Celtics went 25-6 over the rest of the season to finish second in the East.

June 2, 2022 — First Finals appearance: After helping lead the Celtics through the Eastern Conference playoffs, taking out the Nets (sweep), Bucks (seven games), and Heat (seven games), Brown and Boston took on the Warriors in the 2022 NBA Finals.

Brown was one of the stars of a stunning road comeback in Game 1 with 24 points, 7 rebounds, and 5 assists as the Celtics rallied from a 12-point fourth-quarter deficit to steal the opener.

Brown played pretty well in the six-game series, averaging 23.5 points, 7.3 rebounds, and 3.7 assists, but it wasn’t enough to keep Boston from falling to Golden State in six games.

May 10, 2023 — All-NBA honors: Brown was named All-NBA for the first time after the 2022-23 season, earning second team honors after averaging a career-best 26.6 points along with 6.9 rebounds and 3.5 assists.

He had at least 30 points in more than half of Boston’s games as the Celtics went 57-25 in their first season under Joe Mazzulla.

That season ended in playoff disappointment, though, as Boston fell into an 0-3 hole against Miami in the Eastern Conference finals, rallied to force a Game 7, then fell flat in the decider at TD Garden.

Brown struggled in that series against the Heat, averaging just 19 points and shooting a ghastly 7 of 43 (16.3 percent) from 3-point range. He was particularly bad in that Game 7, going 8 of 23 from the field and turning it over eight times.

July 25, 2023 — A record contract: Following a few weeks of silence after he became eligible for a super-max extension, Brown inked a five-year, $304 million deal that was, at the time, the richest in NBA history.

“We’ve got a lot of work to do,” Brown said. “So, let’s get started.”

May 21, 2024 — A clutch shot: After the star-studded Celtics — who added Kristaps Porzingis and Jrue Holiday in the offseason — romped to a 64-18 record and the East’s No. 1 seed in 2023-24, they brushed aside the Heat and Cavaliers, each in five games, to reach the Eastern Conference finals.

Game 1 of that series against the Pacers looked to be spinning away from Boston, which trailed by 3 points with 8 seconds to go.

Then Brown delivered the biggest clutch moment of his Celtics career to date, burying a tough, heavily-contested 3-pointer from the corner to send the game to overtime.

“Before the inbound I was just talking to myself, if I get this shot, it’s going in,” Brown said. “I was telling myself the whole time, if you get it, it’s going up, and it’s going in. I happened to create some space on that backside and was able to make a big time play.

The Celtics won in overtime, then swept the Pacers to return to the NBA Finals. Brown was named Eastern Conference finals MVP after averaging 29.8 points, 5 rebounds, and 3 assists in the series.

June 17, 2024: NBA champion and Finals MVP — The Celtics’ dominant run to the title finished in Game 5 against the Mavericks, with Brown scoring 21 points as Boston won its 18th championship.

After averaging 20.8 points, 5.4 rebounds, and 5 assists in the series, Brown was named NBA Finals MVP, joining a short list of Celtics to win the award with John Havlicek, Jo Jo White, Cedric Maxwell, Larry Bird (twice), and Paul Pierce.

“All of the moments where we came up short, felt like we let the city down, let ourselves down, all of that compiled is how we get to this moment,” Brown said. “And it makes it feel even that much better that we had to go through the journey, the heartbreak, the embarrassment, the loss, to get to the mountaintop.”

May 12, 2025: A dynamic shift — The Celtics were favorites to return to the NBA Finals in 2025, but blew the first two games of a second-round series to the Knicks at home, then lost superstar Jayson Tatum to an Achilles tear in a devastating Game 4.

For the first time, Brown became Boston’s undisputed first option. He stepped up in a big way two days later despite a torn meniscus, racking up 26 points, 12 assists, and 8 rebounds in a Game 5 win to keep the Celtics alive.

It wasn’t enough, though, as Boston was blown out in Game 6, and the franchise’s core was torn down with the summer exodus of Holiday, Porzingis, Al Horford, and Luke Kornet.

“Losing to the Knicks feels like death, but I was always taught that there’s life after death, so we’ll figure out whatever’s next,” Brown said, “I know, Boston, it looks gloomy right now with JT being out and us at the end of the year, but there’s a lot to look forward to, and I want the city to feel excited about that — that this is not the end. I’m looking forward to what’s next.”

Oct. 22, 2025 — A superstar season begins: With Tatum sidelined, Brown had to shoulder the scoring load for 2025-26. He did just that.

Brown averaged 28.7 points, 6.9 rebounds, and 5.1 assists — all career highs — to lead the Celtics to 56 wins. He scored 40-plus points on seven occasions, including a career high-tying 50 against the Clippers in January.

Brown earned second team All-NBA honors for the second time in his career and finished sixth in MVP voting.

May 2, 2026 — One last playoff disappointment: After going up, 3-1, over the 76ers in the first round, the heavily-favored Celtics cratered, blowing that lead for the first time in franchise history and losing Game 7 at home.

Brown started the series hot, but shot just 41.8 percent from the field in the final three games. That Game 7, it turns out, was his last game as a Celtic.

Brown also made some headlines after calling the campaign his “favorite season” despite a first-round exit, a minor controversy that dragged into the summer.

June 23, 2026 — The Giannis trade: Things got uncomfortable as the NBA Draft approached, when it emerged that the Celtics were aggressively pursuing a trade for Bucks superstar Giannis Antetokounmpo. Boston’s offer centered around Brown, but it wasn’t enough to land the two-time MVP, who headed to Miami instead.

That left the Celtics to try to repair the relationship with Brown, who knew the team was actively trying to trade him.

“I don’t love the fact, anytime it’s a big public thing,” said president of basketball operations Brad Stevens.

July 1, 2026 — Traded to Philadelphia: The Celtics agreed to ship Brown to Philadelphia in exchange for Paul George, two first-round picks, and two second-rounders.